United States Court of Appeals

For the First Circuit

No. 19-1971

UNITED STATES OF AMERICA,

Appellee,

v.

JESUS LEONARDO CASTILLO-MARTINEZ,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Nathaniel M. Gorton, U.S. District Judge]

Before

Howard, Chief Judge,

Lynch and Barron, Circuit Judges.

Zainabu Rumala, Assistant Federal Public Defender, for 

appellant.

Karen Eisenstadt, Assistant United States Attorney, with whom 

Alexia R. De Vincentis, Assistant United States Attorney, and 

Andrew E. Lelling, United States Attorney, were on brief, for 

appellee.

October 27, 2021
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LYNCH, Circuit Judge. This case concerns the 

interpretation of a statutory bar in 8 U.S.C. § 1326(d) precluding 

certain collateral attacks in criminal proceedings. Appellant 

Jesus Leonardo Castillo-Martinez falls within the ambit of those 

limitations for the reasons stated below. We affirm the district 

court's denial of his motion to dismiss the criminal proceedings 

against him.

Castillo-Martinez was removed to the Dominican Republic 

in April 2013 after he was convicted in Massachusetts state court 

of illegally distributing marijuana and in New Hampshire state 

court of trafficking OxyContin. He illegally returned to the 

United States and was arrested on August 20, 2016, on a Florida 

fugitive warrant for a new controlled substances offense committed 

in Florida. He was removed again on November 1, 2016. 

On June 23, 2018, after illegally reentering the United 

States again, he was arrested in Massachusetts once more on state 

heroin trafficking charges. He was then federally indicted for 

unlawfully reentering the United States in violation of 8 U.S.C. 

§ 1326(a), which provides that "any alien who (1) has been . . . 

deported, or removed or has departed the United States while an 

order of exclusion, deportation, or removal is outstanding and 

thereafter (2) enters, attempts to enter, or is at any time found 

in, the United States . . . shall be fined under Title 18, or 

imprisoned not more than 2 years, or both." 
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Castillo-Martinez moved to dismiss the indictment under 

8 U.S.C. § 1326(d), making two arguments that the element of 

unlawful reentry was not satisfied because his original removal 

order was not valid. First, he argued that his original removal 

order in 2012 was defective because the Notice to Appear ("NTA") 

he received did not include the time and place of his hearing. 

Second, he argued that his removal order in 2012 was based on the 

classification of his marijuana conviction as an aggravated 

felony, a classification to which he said his immigration counsel 

provided ineffective assistance by not objecting. He then argued 

that the classification was improper under the Supreme Court's 

later decision in Moncrieffe v. Holder, 569 U.S. 184 (2013), issued 

after his removal order. As a result, he argued, the original 

removal order must be declared invalid, and the criminal charges 

for illegal reentry must be dismissed. The district court denied 

Castillo-Martinez's motion. United States v. Castillo-Martinez, 

378 F. Supp. 3d 46, 55 (D. Mass. 2019). 

We affirm.

I.

Castillo-Martinez was born in the Dominican Republic in 

1973 and was admitted to the United States as a lawful permanent 

resident in 1981. In 1996, he was convicted of violating Mass. 

Gen. Laws ch. 94C, § 32C by "knowingly or intentionally 

manufactur[ing], distribut[ing], dispens[ing] or cultivat[ing]" 
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marijuana, a Class D substance under Massachusetts law. For this 

crime, he received a suspended sentence and probation. See id.

§§ 31, 32C. He remained in the United States. 

In February 2011, Castillo-Martinez was indicted by a 

New Hampshire grand jury for conspiring to sell 15,000 tablets of 

OxyContin for approximately $272,000 in violation of N.H. Rev. 

Stat. Ann. § 318-B:2(I). While he was awaiting trial, U.S. 

Immigration and Customs Enforcement ("ICE") lodged a detainer 

against him. He was later convicted of the conspiracy charge in 

June 2012 and received a suspended sentence and probation.1

Shortly after Castillo-Martinez's OxyContin conviction, 

the Department of Homeland Security ("DHS") served him with an NTA 

alleging that he was removable from the United States pursuant to 

8 U.S.C. § 1227(a)(2)(A)(iii) because he had been convicted of an 

aggravated felony. The NTA was based on Castillo-Martinez's 1996 

marijuana conviction and did not state his OxyContin conviction as 

its basis. The NTA did not state a specific date or time for 

Castillo-Martinez's hearing and noted that they were "to be set." 

Castillo-Martinez, acting through counsel, conceded 

removability as alleged in the NTA under the law of the First 

Circuit, which held that his marijuana conviction was an aggravated 

1 Castillo-Martinez received a 576-day credit toward his 

sentence for time served. That 576-day portion of his sentence 

was not suspended. 
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felony. Castillo-Martinez made the counseled choice to apply for 

deferral of removal under the Convention Against Torture ("CAT"). 

He submitted affidavits in support of his CAT petition and 

testified at an immigration hearing. On November 1, 2012, an 

immigration judge ("IJ") denied him CAT relief and ordered that he 

be removed to the Dominican Republic.2 Castillo-Martinez 

unsuccessfully appealed this decision to the Board of Immigration 

Appeals ("BIA") on March 13, 2013, and was removed to the Dominican 

Republic on April 16, 2013. He did not challenge the BIA's 

decision by seeking a petition for review.

Castillo-Martinez returned to the United States at some 

point before April 28, 2016, when he was arrested in Florida on 

another controlled substance charge. He fled Florida, and was 

arrested on August 20, 2016, in Massachusetts pursuant to a 

"Fugitive from Justice" warrant from Florida and was taken into 

administrative custody by ICE. His removal order was reinstated, 

and, on November 1, 2016, he was removed to the Dominican Republic. 

2 The IJ issued a removal order for Castillo-Martinez, 

which resulted in the execution of a "warrant of 

removal/deportation." "We use the terms 'removal' and 

'deportation' interchangeably in this opinion." United States v. 

Luna, 436 F.3d 312, 314 n.1 (1st Cir. 2006). While 8 U.S.C. 

§ 1326(d) refers to deportation orders, it encompasses the change 

in name to removal orders. See United States v. Palomar-Santiago, 

141 S. Ct. 1615, 1619 (2021) (applying 8 U.S.C. § 1326(d) to a 

removal order); Padilla v. Kentucky, 559 U.S. 356, 364 n.6 (2010) 

("The changes to our immigration law have also involved a change 

in nomenclature; the statutory text now uses the term 'removal' 

rather than 'deportation.'").
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Castillo-Martinez returned to the United States again. 

On June 23, 2018, he was arrested in Massachusetts and charged 

with trafficking heroin. On August 2, 2018, he was federally 

indicted for unlawfully reentering the United States in violation 

of 8 U.S.C. § 1326(a).

In February 2019, Castillo-Martinez moved to dismiss the 

unlawful reentry charge. He made two arguments that the unlawful 

reentry element of 8 U.S.C. § 1326(a) was not met because there 

was no valid prior removal order. His first argument was that 

there was no valid prior removal order because under the Supreme 

Court's decision in Pereira v. Sessions, 138 S. Ct. 2105 (2018), 

the fact that the NTA did not include a specific date or time 

deprived the immigration court of jurisdiction and prevented it 

from ordering his removal. His second argument was that there was 

no valid prior removal order based on the Supreme Court's divided 

decision in Moncrieffe, issued shortly after his removal. He 

argued that under Moncrieffe, his marijuana conviction could not 

serve as the basis for his 2012 removal order because that 

conviction was not an aggravated felony, and further that his 

counsel's failure to object on this basis amounted to ineffective 

assistance. 

The government responded to Castillo-Martinez's two 

arguments. As to the second argument, the government relied on 

the statutory limitations on collateral attacks set forth in 8 
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U.S.C. § 1326(d) and specifically argued that he did not fall 

within any of the narrow exceptions that would have permitted a 

collateral attack. Subsection 1326(d) states that in a criminal 

proceeding under 8 U.S.C. § 1326(a), "an alien may not challenge 

the validity of [a] deportation order . . . unless" the alien makes 

three showings: (1) "the alien exhausted any administrative 

remedies that may have been available to seek relief against the 

order"; (2) "the deportation proceedings at which the order was 

issued improperly deprived the alien of the opportunity for 

judicial review"; and (3) "the entry of the order was fundamentally 

unfair." 8 U.S.C. § 1326(d). The government argued that CastilloMartinez failed to exhaust his administrative remedies, that he 

was not denied the opportunity for judicial review, and that the 

removal proceedings were not fundamentally unfair. 

The district court denied the motion. As to CastilloMartinez's first argument, relying on case law from other courts 

of appeals, it held that the IJ had jurisdiction to issue a removal 

order "[b]ecause Castillo-Martinez was served with an NTA 

containing all of the required information and was presumably 

served a separate Notice of Hearing informing him of the time and 

place of his removal hearing (given that he actually appeared at 

that hearing)." Castillo-Martinez, 378 F. Supp. 3d at 53; see 

also Santos-Santos v. Barr, 917 F.3d 486, 490 (6th Cir. 2019); 

Karingithi v. Whitaker, 913 F.3d 1158, 1162 (9th Cir. 2019).
- 8 -

As to his second argument, the district court held that 

Castillo-Martinez had not made the required showings necessary 

under 8 U.S.C. § 1326(d) to collaterally attack the validity of 

his original removal order. Castillo-Martinez, 378 F. Supp. 3d at 

54. First, because Castillo-Martinez "concede[d] that he failed 

to exhaust his administrative remedies and was not denied an 

opportunity for judicial review," the court held that he had not 

satisfied the first two § 1326(d) requirements. See id.; 8 U.S.C.

§ 1326(d)(1)-(2). Next, the court held that even if CastilloMartinez could be excused from meeting some of § 1326(d)'s 

requirements if he could show his counsel had been ineffective, he 

still could not prevail because he had not shown that his counsel's 

performance was deficient or that he was prejudiced by either his 

counsel's actions or the deportation order. Castillo-Martinez, 

378 F. Supp. 3d at 54-55; see also 8 U.S.C. § 1326(d)(3) (requiring 

a showing that "the entry of the [deportation] order was 

fundamentally unfair" to collaterally attack it in a criminal 

proceeding).

Castillo-Martinez pleaded guilty to the unlawful reentry 

charge. He was sentenced to time served and a three-year term of 

supervised release. He reserved the right to appeal the court's 

denial of his motion to dismiss and timely exercised that right. 
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II.

We review de novo the legal conclusions underlying the 

district court's denial of Castillo-Martinez's motion to dismiss. 

See United States v. Mendoza, 963 F.3d 158, 161 (1st Cir. 2020),

cert. denied sub nom. Mendoza-Sanchez v. United States, 141 S. Ct. 

834 (2020). We review its factual findings for clear error and 

its "ultimate ruling" for abuse of discretion. See id. (quoting 

United States v. Doe, 741 F.3d 217, 226 (1st Cir. 2013)). On 

appeal, Castillo-Martinez renews the two main arguments he made to 

the district court. 

A.

Castillo-Martinez's first argument, based on Pereira, 

has already been considered and rejected by the First Circuit since 

the district court's ruling. See Mendoza, 963 F.3d at 161 ("We 

have already squarely rejected the contention that the omission of 

the initial hearing date and time in a notice to appear deprives 

the immigration court of jurisdiction over a removal 

proceeding."); Goncalves Pontes v. Barr, 938 F.3d 1, 6-7 (1st Cir. 

2019).3 It fails for this reason.

3 Castillo-Martinez submitted a Rule 28(j) letter saying 

that the Supreme Court's recent decision in Niz-Chavez v. Garland, 

141 S. Ct. 1474 (2021), supported his argument. Niz-Chavez dealt 

with whether an NTA that did not include certain information 

triggered the Illegal Immigration Reform and Immigrant 

Responsibility Act's stop-time rule. See id. at 1479. The Court 

described a "notice to appear" in a removal proceeding as a single 

"case-initiating document," id. at 1482, but it did not suggest 
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B.

Castillo-Martinez's second argument is based on 

Moncrieffe and his contention that he satisfies the conditions 

under § 1326(d), which would permit him to collaterally attack his 

prior removal. Subsection 1326(d) starts with a prohibition on 

such collateral attacks, stating that in a § 1326(a) criminal 

proceeding, "an alien may not challenge the validity of [a] 

deportation order." The subsection then sets forth an exception 

in an "unless" clause, providing that an alien may not bring a 

collateral attack unless the alien satisfies three conditions: 

(1) "the alien exhausted any administrative remedies that may have 

been available to seek relief against the order"; (2) "the 

deportation proceedings at which the order was issued improperly 

deprived the alien of the opportunity for judicial review"; and 

(3) "the entry of the order was fundamentally unfair." 8 U.S.C. 

§ 1326(d).4 

that a single-document NTA is also required to establish 

jurisdiction. Thus, we remain bound by our holding in Mendoza

that "jurisdiction of an immigration court is governed by agency 

regulation, not by [statute]. . . ." 963 F.3d at 161 (internal 

citations omitted); see Maniar v. Garland, 998 F.3d 235, 242 & n.2 

(5th Cir. 2021) (explaining that Niz-Chavez does not affect its 

prior holding that an immigration court's jurisdiction is governed 

by federal regulations and that an NTA without date or time 

information is sufficient to confer jurisdiction).

4 Congress passed § 1326(d) with the intent of insulating 

removal orders against collateral attacks in criminal proceedings, 

emphasizing the importance of finality and deference to 

immigration agency determinations while guaranteeing minimal due 

process. See 140 Cong. Rec. S28440-41 (daily ed. Oct. 6, 1994) 
- 11 -

The district court was correct that Castillo-Martinez 

has not met any of the three statutory requirements. He has not 

exhausted the administrative remedies for his newly raised 

ineffective assistance claim. Judicial review was plainly 

available. The 2012 removal proceeding was not fundamentally 

unfair.

1.

Castillo-Martinez fails to satisfy the first two 

statutory requirements of § 1326(d). He neither exhausted his 

administrative remedies nor was he deprived of an opportunity for 

judicial review. As the Supreme Court recently emphasized, "each 

of the statutory requirements of § 1326(d) is mandatory." United 

States v. Palomar-Santiago, 141 S. Ct. 1615, 1622 (2021). 

(statement of Sen. Smith) (stating that the language of § 1326(d) 

"which is taken directly from the U.S. Supreme Court case of United 

States v. Mendoza-Lopez, 481 U.S. 828 (1987), is intended to ensure 

that minimum due process is followed in the original deportation 

proceeding while preventing wholesale, time-consuming attack on 

underlying deportation orders.").

In civil proceedings, a noncitizen who reenters the 

United States illegally after having previously been ordered 

removed may not challenge the original removal order at all if 

that original order is reinstated. 8 U.S.C. § 1231(a)(5). 

Subsection 1231(a)(5) provides that the reinstated order "is not 

subject to being reopened or reviewed," and the noncitizen "is not 

eligible and may not apply for any relief" from the order. Id. 

Subsection 1231(a)(5) underscores the importance of the finality 

of a removal order once entered. There is no reason to think that 

Congress intended a lesser degree of finality in criminal cases 

than in civil cases.
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We may affirm a district court's decision based on any 

independent ground supported by the record, even if the district 

court did not reach the issue. See United States v. Cabrera-Polo, 

376 F.3d 29, 31 (1st Cir. 2004) ("We are not committed to the 

district court's reasoning, but, rather, may affirm its order on 

any independent ground made apparent by the record."); see also

Dimott v. United States, 881 F.3d 232, 238-40 (1st Cir. 2018).

Castillo-Martinez conceded that he has not met the first 

two § 1326(d) requirements in the traditional sense. See CastilloMartinez, 378 F. Supp. 3d at 54. The Supreme Court issued its 

decision in Moncrieffe on April 23, 2013, shortly after CastilloMartinez's first removal. Between April 2013 and February 2019, 

when he moved to dismiss the unlawful reentry charge, CastilloMartinez never once filed a motion to reopen his 2012 removal 

proceedings based on ineffective assistance of counsel in light of 

Moncrieffe. See 8 U.S.C. § 1229a(c)(7).5

We have long recognized the exhaustion requirement as an 

important element of the § 1326(d) requirements for an alien to 

collaterally attack a removal order. See United States v. Luna, 

436 F.3d 312, 317 (1st Cir. 2006). This exhaustion requirement is 

5 Motions to reopen removal hearings are disfavored 

because of "the compelling public interests in finality and the 

expeditious processing of proceedings." Muyubisnay-Cungachi v. 

Holder, 734 F.3d 66, 71 (1st Cir. 2013) (quoting Raza v. Gonzales, 

484 F.3d 125, 127 (1st Cir. 2007)).
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consistent with the congressional intent underlying § 1326(d) to 

defer to agency determinations and restrict collateral attacks on 

those agency determinations. 

Castillo-Martinez nevertheless argues that if he can 

show that his counsel was ineffective, we should excuse his failure 

even where he failed to exhaust his ineffective assistance claim 

before the BIA. We do not accept his proposition, though we 

acknowledge that some circuits adopted this approach before the 

Supreme Court's recent decision in Palomar-Santiago. See United 

States v. Lopez-Chavez, 757 F.3d 1033, 1044 (9th Cir. 2014)

(holding that the first two § 1326(d) requirements were satisfied 

because "counsel's ineffectiveness . . . caused [defendant's] 

failure to exhaust administrative remedies and deprived him of his 

opportunity for judicial review"); United States v. Cerna, 603 

F.3d 32, 40 (2d Cir. 2010) (holding that ineffective assistance of 

counsel may be grounds to excuse § 1326(d)(2)'s requirement). 

The text of § 1326(d) and the Supreme Court's decision 

in Palomar-Santiago do not support excusing Castillo-Martinez's 

failure to satisfy the statutory requirements. In PalomarSantiago, the unanimous Court answered the statutory question 

before it by holding that the "first two procedural requirements 

are not satisfied just because a noncitizen was removed for an 

offense that did not in fact render him removable." PalomarSantiago, 141 S. Ct. at 1621. The Ninth Circuit's contrary holding 
- 14 -

was "incompatible with the text of § 1326(d)." Id. at 1620. The 

Court held that "[w]hen Congress uses 'mandatory language' in an 

administrative exhaustion provision, 'a court may not excuse a 

failure to exhaust.'" Id. at 1621 (quoting Ross v. Blake, 136 S. 

Ct. 1850, 1857 (2016)) (emphasis added). That is exactly what 

Castillo-Martinez asks us to do. He concedes that he has not met 

the first two § 1326(d) requirements but asks us to excuse those 

failures. See Ross, 136 S. Ct. at 1856 (holding that, other than 

the requirement that a remedy be "available," the text of the 

Prison Litigation Reform Act ("PLRA") "suggests no limits on an 

inmate's obligation to exhaust -- irrespective of any 'special 

circumstances'").

The Supreme Court rejected Palomar-Santiago's 

counterargument that he should be excused from showing the first 

two procedural requirements of § 1326(d) because further 

administrative review of a removal was not "available" when the IJ 

erroneously informed him that his prior conviction rendered him 

removable. Palomar-Santiago, 141 S. Ct. at 1621 ("Noncitizens, 

the argument goes, cannot be expected to know that the immigration 

judge might be wrong."). The Court found that administrative 

review and judicial review of the removal were not "unavailable." 

Id. The Court reasoned that "[a]dministrative review of removal 

orders exists precisely so noncitizens can challenge the substance 

of immigration judges' decisions." Id. The Court further stated 
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that "[t]he immigration judge's error on the merits does not excuse 

the noncitizen's failure to comply with a mandatory exhaustion 

requirement if further administrative review, and then judicial 

review if necessary, could fix that very error." Id.

This reasoning applies equally to Castillo-Martinez. 

The BIA "provides a process for adjudicating ineffective

assistance of counsel claims through a motion to reopen." 

Gicharu v. Carr, 983 F.3d 13, 17 (1st Cir. 2020). CastilloMartinez does not explain why he never moved to reopen his removal 

proceedings after Moncrieffe. The ninety-day deadline for filing 

such a motion, see 8 C.F.R. § 1003.23(b)(1), does not render relief 

via a motion to reopen unavailable. As this court has previously 

explained, "[t]he BIA . . . entertains claims for equitable tolling 

of the filing deadline for motions to reopen where it is alleged 

that ineffective assistance of counsel caused the motion to be 

untimely." Gicharu, 983 F.3d at 17 (citing Pineda v. Whitaker, 

908 F.3d 836, 840-41 (1st Cir. 2018)). Even if "the standard for 

establishing equitable tolling is daunting, it does not render 

review by the BIA . . . unavailable." Id. at 18 (internal citation 

omitted); cf. Ross, 136 S. Ct. at 1858 (explaining that the PLRA's 

exhaustion requirement "hinges on the 'availab[ility]' of 

administrative remedies" because "[a]n inmate . . . must exhaust 

available remedies[] but need not exhaust unavailable ones").
- 16 -

Ordinarily, an alien raising an ineffective assistance 

of counsel claim through a motion to reopen must comply with the 

procedural requirements set forth in the leading BIA case Matter 

of Lozada, 19 I. & N. Dec. 637 (BIA 1988):

(1) an affidavit explaining the petitioner's 

agreement with counsel regarding legal 

representation; (2) evidence that counsel has 

been informed of the allegations of 

ineffective assistance and has had an 

opportunity to respond; and (3) if it is 

asserted that counsel's handling of the case 

involved a violation of ethical or legal 

responsibilities, a complaint against the 

attorney filed with disciplinary authorities 

or, in the alternative, an explanation for why 

such a complaint has not been filed.

Ferreira v. Barr, 939 F.3d 44, 46 (1st Cir. 2019) (quoting Pineda, 

908 F.3d at 839 n.2); see Lozada, 19 I. & N. Dec. at 639; see also

Pineda, 908 F.3d at 839 n.2 ("The BIA's decision in Lozada is 

widely recognized as a leading case with respect to claims of 

ineffective assistance of counsel in the immigration context."). 

We have recognized that the Lozada requirements are "designed to 

give the BIA sufficient information to inform its decision without 

resorting to an evidentiary hearing." Ferreira, 939 F.3d at 46. 

In the BIA's view, false claims of ineffective assistance can be 

identified by a counsel's response to the notification or the 

alien's insufficiently explained refusal to file a formal 

complaint against that counsel. Saakian v. INS, 252 F.3d 21, 26 

(1st Cir. 2001). These requirements lessen the chances of 
- 17 -

meritless claims and make it easier for the BIA to act on 

meritorious claims of ineffective assistance. Id.

Once the procedural requirements are satisfied, the BIA 

reviews ineffective assistance claims for two substantive 

requirements: (1) immigration counsel's performance was deficient; 

and (2) immigration counsel's performance caused prejudice to the 

client. See Matter of Melgar, 28 I. & N. Dec. 169, 171 (BIA 2020); 

Lozada, 19 I. & N. Dec. at 638.

After the BIA issues its decision, an alien may then 

file a petition for review with our court. When reviewing the 

BIA's decisions, we uphold findings of fact about ineffective 

assistance "as long as they are supported by substantial evidence 

on the record as a whole." Ferreira, 939 F.3d at 45. We review 

the BIA's denial of a motion to reopen for ineffective assistance 

for abuse of discretion. Muyubisnay-Cungachi v. Holder, 734 F.3d 

66, 70 (1st Cir. 2013).

Castillo-Martinez and the dissent would have us bypass 

this process entirely and in doing so, alter our standard of review 

from the substantial evidence standard to de novo review of 

fundamental fairness concerns. The dissent's approach would have 

us decide de novo, without record support, whether counsel's 

conduct constituted ineffective assistance. Subsection 1326(d) 

does not allow for this. The ability to assert an ineffective

assistance of counsel claim to the BIA was available to Castillo-
- 18 -

Martinez well before his February 2019 motion to dismiss his 

unlawful reentry charge. He failed to exhaust any such claim 

before the agency.

2.

Even assuming dubitante that Castillo-Martinez can 

satisfy § 1326(d)'s first two requirements despite his failure to 

move to reopen his removal proceedings or assert an ineffective 

assistance claim to the agency, he has not shown that "the entry 

of the order was fundamentally unfair." 8 U.S.C. § 1326(d)(3). 

Castillo-Martinez argues that he can satisfy this third 

requirement of § 1326(d) by demonstrating ineffective assistance 

of counsel, but he has not met his burden of showing that his 

immigration counsel was ineffective on the record before us.

Aliens in removal proceedings are not defendants in 

criminal proceedings. The same rules do not apply. See Ferreira, 

939 F.3d at 46 n.1. For example, aliens in removal proceedings 

have no Sixth Amendment right to counsel. See id.; Saakian, 252 

F.3d at 24. In his removal proceeding, Castillo-Martinez sought 

a benefit from the government: to remain in the country. The 

proceeding was not to determine whether his liberty would be 

involuntarily restrained; indeed, he remained free to depart on 

his own at any time. It is true that under Reno v. Flores, removal 

proceedings must comport with the fundamental requirements of the 

Due Process Clause under the Fifth Amendment. 507 U.S. 292, 306 
- 19 -

(1993). Accordingly, his burden of showing ineffective assistance 

of counsel in his removal proceeding is different than the burden 

put on criminal defendants under Strickland. Cf. Strickland v. 

Washington, 466 U.S. 668, 687 (1984). We have held that 

"[i]neffective assistance of counsel in a deportation proceeding 

is a denial of due process under the Fifth Amendment if the 

proceeding was so fundamentally unfair that the alien was prevented 

from reasonably presenting his case." Fustaguio Do Nascimento v. 

Mukasey, 549 F.3d 12, 17 (1st Cir. 2008) (quoting Rodríguez–

Lariz v. INS, 282 F.3d 1218, 1226 (9th Cir. 2002)). To establish 

that a proceeding was fundamentally unfair because of ineffective 

assistance of immigration counsel, an alien must show "[1] a 

deficient performance by counsel and [2] 'a reasonable probability 

of prejudice resulting from [his] former representation.'" 

Muyubisnay-Cungachi, 734 F.3d at 72 (quoting Zeru v. Gonzales, 503 

F.3d 59, 72 (1st Cir. 2007)).

Castillo-Martinez cannot meet that standard before the 

BIA, nor can he meet that standard before this court.

i.

Even on review of the record before us, CastilloMartinez has not shown that his counsel at the removal proceeding 

was deficient. Castillo-Martinez argues that his counsel "was 

ineffective in conceding that Castillo-Martinez's marijuana 

offense qualified as an aggravated felony." His counsel's 
- 20 -

strategic concession was based on longstanding and controlling 

First Circuit precedent. See Julce v. Mukasey, 530 F.3d 30, 35 

(1st Cir. 2008), abrogated by Moncrieffe, 569 U.S. at 187. Absent 

"unusual circumstances," "the case law is clear that an attorney's 

assistance is not rendered ineffective because he failed to 

anticipate a new rule of law." Powell v. United States, 430 F.3d 

490, 491 (1st Cir. 2005) (quoting Kornahrens v. Evatt, 66 F.3d 

1350, 1360 (4th Cir. 1995)).

Any ineffective assistance of counsel claim is also 

defeated by the fact that Castillo-Martinez's counsel had 

strategic reasons for conceding removability. In addition to the 

marijuana conviction, Castillo-Martinez was convicted of 

conspiracy to sell OxyContin under N.H. Rev. Stat. Ann. § 318-

B:2(I) before the government sent him an NTA. This conviction 

qualifies as an aggravated felony and would have provided a 

standalone basis for mandatory removal. See 8 U.S.C. § 1227(a); 

id. § 1227(a)(2)(A)(iii).6 Castillo-Martinez's counsel may have 

6 To decide if a state conviction qualifies as an 

aggravated felony under the Immigration and Nationality Act 

("INA"), we "employ a 'categorical approach' to determine whether 

the state offense is comparable to an offense listed in the INA." 

Moncrieffe, 569 U.S. at 190. Under this approach, we determine if 

"'the state statute defining the crime of conviction' 

categorically fits within the 'generic' federal definition of a 

corresponding aggravated felony." Id. at 190 (quoting Gonzales v. 

Duenas-Alvarez, 549 U.S. 183, 186 (2007)). 

Under the INA, an aggravated felony includes "illicit 

trafficking in a controlled substance (as defined in [21 U.S.C. § 

802]), including a drug trafficking crime (as defined in [18 U.S.C. 
- 21 -

correctly concluded that even after predicting the Supreme Court 

would overturn controlling First Circuit precedent in Moncrieffe, 

any objection on this basis would be futile given Castillo-

§ 924(c)]." 8 U.S.C. § 1101(a)(43)(B). A drug trafficking crime 

is "any felony punishable under the Controlled Substances Act 

[("CSA")]." 18 U.S.C. § 924(c)(2). Under the CSA, it is a felony 

"to manufacture, distribute, or dispense, or possess with intent 

to manufacture, distribute, or dispense, a controlled substance," 

21 U.S.C. § 841(a)(1), if the "maximum term of imprisonment 

authorized" is more than one year, 18 U.S.C. § 3559(a)(5); see

Moncrieffe, 569 U.S. at 188.

In United States v. Burghardt, 939 F.3d 397, 406-09 (1st 

Cir. 2019), applying the categorical approach, this court held 

that because the elements of selling a controlled substance under 

N.H. Rev. Stat. Ann. § 318-B:2(I) were not broader than the 

elements of the generic "serious drug offense" defined in the Armed 

Career Criminal Act, a § 318-B:2(I) conviction for selling drugs 

is a "serious drug offense." Id. A "serious drug offense" 

includes "an offense under State law, involving manufacturing, 

distributing, or possessing with intent to manufacture or 

distribute, a controlled substance (as defined in [21 U.S.C. 

§ 802]), for which a maximum term of imprisonment of ten years or 

more is prescribed by law." 18 U.S.C. § 924(e)(2)(A)(ii). 

As is clear from their respective definitions, serious 

drug offenses under 18 U.S.C. § 924(e)(2)(A)(ii) are a subset of 

drug trafficking crimes as defined by 18 U.S.C. § 924(c). This 

means that a serious drug offense is necessarily a drug trafficking 

crime, and a drug trafficking crime is necessarily an aggravated 

felony. It follows that Castillo-Martinez's § 318-B:2(I) 

conviction is an aggravated felony under the INA and would have 

precluded him from receiving various types of discretionary relief 

from the removal order. See United States v. Hercules, 947 F.3d 

3, 8 (1st Cir. 2020) (stating that "appellant's aggravated felony 

convictions render him ineligible for various forms of relief from 

removal," including cancellation of removal, 8 U.S.C. 

§ 1229b(a)(3), and asylum, id. § 1158(b)(2)(A)(ii), (B)(i)).

Castillo-Martinez was convicted of conspiracy to sell OxyContin, 

but "conspiracy to commit an offense described in [8 U.S.C. § 

1101(a)(43)]" is also an aggravated felony. 8 U.S.C. § 

1101(a)(43)(U).
- 22 -

Martinez's other drug conviction. See Knowles v. Mirzayance, 556 

U.S. 111, 126-27 (2009).

That counsel was making a strategic choice is shown by 

the fact that Castillo-Martinez applied for deferral of removal 

under the CAT and submitted affidavits and testimony from himself 

and his sister in support. Castillo-Martinez's counsel was not 

deficient because he elected to focus on one defense to removal 

rather than another defense that he reasonably perceived as weak. 

This is not a case where counsel gave up "the only defense 

available." Knowles, 556 U.S. at 126-27 ("Counsel also is not 

required to have a tactical reason . . . for recommending that a 

weak claim be dropped altogether.").7

7 There was a second strategic choice involved. An alien 

previously ordered removed because of an aggravated felony 

conviction is not eligible to seek readmission for 20 years. See

8 U.S.C. § 1182(a)(9)(A)(i); 8 C.F.R. § 212.2(a). Prior to the 

completion of the 20-year absence, an alien may apply for a 

discretionary I-212 waiver, or "permission to reapply." See 8 

U.S.C. § 1182(d)(3); 8 C.F.R. §§ 212.2(a), 212.4. Counsel could 

have easily concluded that Castillo-Martinez would be removed 

based on either drug conviction. Had counsel objected to the 

marijuana conviction as the basis for the removal order or 

requested a stay pending the Supreme Court's decision in 

Moncrieffe, this would have only prolonged the removal 

proceedings. Counsel did not know when the Supreme Court would 

issue its decision in Moncrieffe, and the government could have 

amended the NTA to include the Oxycontin conviction, thus 

prolonging the removal proceedings further. See 8 C.F.R. 

§ 1240.10(e). Any delay in removal would also delay the running 

of Castillo-Martinez's 20-year absence requirement.
- 23 -

ii.

Castillo-Martinez also cannot show prejudice resulting 

from his immigration counsel's actions. See Muyubisnay-Cungachi, 

734 F.3d at 72.

Even if Castillo-Martinez's marijuana conviction had not 

been classified as an aggravated felony, he has failed to show 

that there is a reasonable probability he would not have been 

removed because of that conviction. As a controlled substance 

offender under 8 U.S.C. § 1227(a)(2)(B)(i), he would have had to 

apply for and receive discretionary relief to avoid deportation. 

See Moncrieffe, 569 U.S. at 204 (2013) ("Escaping aggravated felony 

treatment does not mean escaping deportation . . . It means only 

avoiding mandatory removal."); United States v. Soto-Mateo, 799 

F.3d 117, 123 (1st Cir. 2015) (explaining that "even if the 

appellant's prior convictions did not comprise aggravated 

felonies, he would not have been entitled as of right to remain in 

the United States" and holding that there is no "constitutional 

right to be . . . considered for . . . discretionary relief"); 8 

U.S.C. § 1229b(a). Castillo-Martinez has made no argument that he 

would have applied for such discretionary relief, let alone has he 

offered any affirmative reasons why that relief would have been 

warranted. His drug convictions prior to the entry of his 

deportation order and "the relative lack of positive equities 
- 24 -

eliminate any reasonable likelihood that he would have received a 

grant of relief." Luna, 436 F.3d at 323.

Castillo-Martinez also has not shown that he would not 

have been subject to mandatory removal because of his separate 

OxyContin conviction. Even if he had successfully challenged the 

earlier aggravated felony classification for his Massachusetts 

offense, the government could have freely amended the NTA to 

include other grounds for removal. Federal regulations say that 

"[a]t any time during the proceeding" the government may lodge 

"additional or substituted charges of inadmissibility and/or 

deportability and/or factual allegations." 8 C.F.R. § 1240.10(e). 

"[T]here is no requirement that the [government] advance every 

conceivable basis for deportability" in the original NTA. 

Magasouba v. Mukasey, 543 F.3d 13, 16 (1st Cir. 2008) (per curiam) 

(second alteration in original) (quoting De Faria v. INS, 13 F.3d 

422, 424 (1st Cir. 1993) (per curiam)). The government is also 

allowed to replace all of the original charges in the NTA with new 

ones, see Cheung v. Holder, 678 F.3d 66, 70 n.6, 70-71 (1st Cir. 

2012), and "reopen . . . deportation proceedings to consider . . . 

substitute charges" against an alien if the convictions underlying 

the original charges have been vacated, De Faria, 13 F.3d at 424. 

iii.

Castillo-Martinez fails to satisfy the distinct 

statutory prejudice requirement under § 1326(d)(3), which 
- 25 -

separately requires a "showing of prejudice." Soto-Mateo, 799 

F.3d at 124. "[S]uch a showing entails 'a reasonable likelihood 

that the result would have been different if the error in the 

deportation proceeding had not occurred.'" Id. (quoting Luna, 436 

F.3d at 321).

Castillo-Martinez argues that the district court's 

prejudice analysis is incorrect because we must focus only on the 

basis for removal cited in his original NTA for his 2012 removal 

order. He says that because his NTA included only his marijuana 

conviction and specifically said it was an aggravated felony under 

8 U.S.C. § 1227(a)(2)(A)(iii), "[o]ther grounds for removal are 

not relevant to the instant question of prejudice."8

We review whether entry of the removal order was 

fundamentally unfair. See United States v. Martinez-Hernandez, 

8 In support of this argument, Castillo-Martinez cites 

SEC v. Chenery Corp., 332 U.S. 194, 196 (1947), which says we are 

"powerless to affirm the administrative action by substituting 

what [we] consider[] to be a more adequate or proper basis." He 

also cites cases from the Ninth Circuit supporting his 

understanding of the prejudice analysis. See, e.g., United 

States v. Camacho-Lopez, 450 F.3d 928, 930 (9th Cir. 2006) 

("[Defendant's] Notice to Appear charged him as removable only for 

having committed an aggravated felony . . . [because his] prior 

conviction did not fit that definition[, he] was removed when he 

should not have been and clearly suffered prejudice.").

Chenery is inapposite because we are not affirming his 

removal order or the basis for its entry. We are reviewing the 

district court's rejection of his collateral attack on the order 

and considering whether entry of the deportation order was 

fundamentally unfair. See United States v. Martinez-Hernandez, 

932 F.3d 1198, 1204 (9th Cir. 2019). 
- 26 -

932 F.3d 1198, 1204 (9th Cir. 2019). In doing so, we must consider 

other grounds available to the government that would also have 

supported entry of the removal order. We assess then the chances 

of Castillo-Martinez receiving relief from removal. See United 

States v. Almanza-Vigil, 912 F.3d 1310, 1323 n.10 (10th Cir. 2019) 

(explaining that 8 U.S.C. § 1326(d)(3) "prohibits us from 

addressing the removal order itself unless [the defendant] can 

establish that the order's entry was fundamentally unfair," and 

"the fundamental-unfairness inquiry hinges on [the defendant's] 

chances of receiving relief from removal"). We assess CastilloMartinez's chances of relief from removal as a key part of the due 

process fundamental unfairness inquiry embodied in the statutory 

bar to such collateral attacks. Here, Castillo-Martinez's chances 

of relief from removal were nonexistent. His outstanding New 

Hampshire Oxycontin conviction was not a small offense. He 

conspired to distribute more than 15,000 OxyContin tablets for 

over $270,000. He was a dealer of a drug plaguing New Hampshire. 

It is inconceivable that the government would not have amended his 

removal order to add the more serious OxyContin conviction if the 

marijuana conviction could not serve as a basis for removal.

3.

We respond below in greater detail to the dissent.9

9 We note at the outset that the government did not waive 

its arguments as to whether Castillo-Martinez satisfied the first 
- 27 -

The dissent objects to our consideration that CastilloMartinez's counsel made a strategic choice not to object and to 

instead apply for deferral of removal under the CAT. The dissent 

states that Castillo-Martinez "was not apprised at any prior point 

in the litigation that [this ground] was even in dispute." But it 

is Castillo-Martinez who bears the burden of demonstrating that 

his immigration counsel provided assistance so ineffective as to 

violate the Constitution. He has the burden as to the totality of 

two statutory requirements of § 1326(d). In the district court, 

the government argued that Castillo-Martinez both failed to 

exhaust his administrative remedies and that he was not denied the 

opportunity for judicial review. On appeal, the government 

maintains the same position and argues that our circuit has not 

recognized an exception to the statutory exhaustion requirement 

and need not do so in this case. The government's brief continues 

with language that deliberately does not concede these arguments: 

"Even assuming such an exception exists, Castillo-Martinez has not 

established that he would be entitled to it." An "assuming 

arguendo" statement is not a concession and not a waiver.

Waiver is "treated as an 'intentional,' and therefore 

permanent, abandonment of a position." United States v. TorresRosario, 658 F.3d 110, 115 (1st Cir. 2011) (quoting United 

States v. Walker, 538 F.3d 21, 22 (1st Cir. 2008)). There was no 

intentional abandonment by the government here. As such, there 

was no waiver.

Further, even if there had been a waiver, we do not 

"'religiously' hold[] waiver against the Government" where the 

government focuses its argument on one procedural bar rather than 

another. Dimott, 881 F.3d at 238-40 (holding that federal courts 

may raise sua sponte procedural arguments not raised by the 

government). "[W]e have discretion to overlook waiver by the 

government in a criminal case when circumstances justify us in 

doing so." United States v. Carrasco-De-Jesús, 589 F.3d 22, 26 

n.1 (1st Cir. 2009); see United States v. Borrero-Acevedo, 533 

F.3d 11, 15 n.3 (1st Cir. 2008) ("This court is not bound by a 

party's concessions.").
- 28 -

his counsel's actions in the immigration proceedings. See

Muyubisnay-Cungachi, 734 F.3d at 72. Castillo-Martinez had 

numerous opportunities to address this ground, including by 

raising the issue of ineffective assistance before the 

administrative agency, which he failed to do.

The dissent also misunderstands the scope of our review 

under 8 U.S.C. § 1326(d). Congress did not adopt the dissent's 

reading of United States v. Mendoza-Lopez, 481 U.S. 828 (1987), in 

passing § 1326(d). Rather, § 1326(d) makes clear that CastilloMartinez "may not challenge the validity of the deportation order" 

unless he first demonstrates that "the entry of the order was 

fundamentally unfair." 8 U.S.C. § 1326(d). When Congress used 

the phrase "fundamentally unfair" in § 1326(d)(3), it meant that 

aliens must show that they have been denied due process under the 

Fifth Amendment. See United States v. Torres, 383 F.3d 92, 103 

(3d Cir. 2004) (collecting cases and noting that "[i]n measuring 

whether an alien's removal proceeding was 'fundamentally unfair,' 

most circuits ask whether the alien was denied due process"). To 

establish a due process violation, an alien must show both 

procedural error and prejudice.10 See Luna, 436 F.3d at 319 

10 We have recognized that "[t]here may be some cases where 

the agency's violation of a petitioner's rights was 'so flagrant, 

and the difficulty of proving prejudice so great' that prejudice 

may be presumed." Luna, 436 F.3d at 321 n.14 (quoting United 

States v. Loaisiga, 104 F.3d 484, 488 (1st Cir. 1997)). Those 

circumstances would be akin to structural errors in the criminal 
- 29 -

("[C]ourts uniformly require a showing of procedural error and 

prejudice" under §1326(d)(3)); cf. United States v. Marcus, 560 

U.S. 258, 264-5 (2010) (explaining in the criminal context that 

the Court has "insisted upon a showing of individual prejudice" 

for a claim of non-structural error under the Due Process Clause); 

Strickland, 466 U.S. at 696 (stating that ineffective assistance 

claims under the Sixth Amendment require a showing of deficient 

performance and prejudice and that "the ultimate focus of inquiry 

must be on the fundamental fairness of the proceeding whose result 

is being challenged."). Interpreting § 1326(d)'s "fundamentally 

unfair" language to require a due process violation is consistent 

with Congress's goal of making it more difficult for aliens to

collaterally attack their removal orders. See H.R. Rep. No. 104-

22, at 16 (1995) (noting that the Criminal Alien Deportation 

Improvements Act "amends the INA to provide that the alien charged 

with [illegal reentry] may only challenge the validity of the 

original deportation order" if § 1326(d)'s conditions are met). 

The dissent misreads the significance of the definite 

article "the" and in doing so, renders the two separate prejudice 

requirements, under the ineffective assistance standard and the 

§ 1326(d) fundamental unfairness standard, meaningless. Under the 

context. See Weaver v. Massachusetts, 137 S. Ct. 1899, 1905 (2017) 

(describing a "structural error" as "an error entitling the 

defendant to automatic reversal without any inquiry into 

prejudice"). That is not this case.
- 30 -

dissent's approach, we would be limited to looking at the basis of 

the original order and not any other grounds for removal that would 

have supported entry of the removal order.11 This interpretation 

of § 1326(d) could be satisfied by the showing of any error in the 

original order, thereby reading out both prejudice requirements 

entirely. 

The dissent's prejudice conclusion also improperly 

focuses on the specific ground for the removal order rather than 

looking at the entire context of the removal proceeding. In 

criminal proceedings, the prejudice analysis requires that a 

defendant show that "[i]t must be reasonably likely that the result 

of the criminal proceeding would have been different if counsel 

had performed as the defendant asserts he should have." Rivera11 Even if we were limited to Castillo-Martinez's original 

removal order, the IJ acknowledged Castillo-Martinez's Oxycontin

conviction and recognized that it would serve as a basis for 

mandatory removal. The IJ wrote in that removal order:

The Respondent has criminal convictions from 

1996 for the Manufacture, Distribution, and 

Cultivation of Marijuana, for which he 

received a sentence of two years in a house of 

corrections. This is an aggravated felony, 

which comprises the basis for removal. In 

addition, more recently, the Respondent was 

convicted this year for a 2010 violation in 

Rockingham, New Hampshire, for Possession and 

Sale of a Narcotic Drug and the Conspiracy 

Thereof, for which he received again a two 

year suspended sentence. This, too, is a drug 

trafficking offense constituting an 

aggravated felony.
- 31 -

Rivera v. United States, 827 F.3d 184, 187 (1st Cir. 2016) 

(quotations omitted). "[T]hat likelihood 'must be substantial, 

not just conceivable.'" Hensley v. Roden, 755 F.3d 724, 736 (1st 

Cir. 2014) (quoting Harrington v. Richter, 562 U.S. 86, 112 

(2011)). Here, Castillo-Martinez has not shown that there is a 

substantial likelihood that the result of the removal proceeding 

would have been different. The IJ in Castillo-Martinez's original 

removal order specifically acknowledged that the OxyContin 

conviction "too, is a drug trafficking offense constituting an 

aggravated felony." Even if Castillo-Martinez's marijuana 

conviction had not been classified as an aggravated felony, the 

result of the proceeding would have been the same -- a removal 

order -- even if the ground supporting the entry of that removal 

order may have been different.

Our holding in Williams v. United States, 858 F.3d 708, 

716 (1st Cir. 2017), is instructive as to the scope of the 

applicable prejudice analysis. In that case, Williams was charged 

in New Hampshire under 18 U.S.C. § 1542 for committing passport 

fraud. New Hampshire was an improper venue for this charge but a 

proper venue for the related, uncharged offense of making a 

material false statement in violation of 18 U.S.C. § 1001. 

Williams told his counsel that he "wanted the case to be dismissed" 

because venue was improper. Id. at 712. Instead, his counsel 

consented to the government's filing of a superseding indictment 
- 32 -

replacing the § 1542 charge with a charge under § 1001. Williams 

eventually pleaded guilty to the § 1001 charge in New Hampshire, 

but he argued that, but-for his counsel's concession, the

government would have had to bring a new charge and he could have 

transferred the case to his hometown in New York instead of being 

forced to defend it in New Hampshire. Id. at 716. Specifically, 

he argued that "the initial result of the proceeding would have 

been different because the § 1542 charge for passport fraud would 

have been dismissed." Id.

In conducting the prejudice analysis, we did not focus 

narrowly on whether the original charge against Williams would 

have been dismissed (as Castillo-Martinez would have us do here). 

Instead, we focused more broadly on the likely result of the 

proceeding, holding that it "would have been no different had his 

counsel not agreed with the government's wish to file a superseding 

indictment" because he would have eventually been charged and 

convicted under § 1001 in either New Hampshire or New York, even 

if the government would have had to file new charges in a new 

indictment. Id. So too here: Castillo-Martinez cannot show 

prejudice because, regardless of whether his counsel had asked the 

court to delay the proceedings pending Moncrieffe, it is likely a 

removal order would have been entered against him. 

The dissent, in several ways, is inconsistent with the 

congressional intent underlying § 1326(d). First, the dissent's 
- 33 -

reading eliminates the exhaustion requirement, including the BIA's 

Lozada requirements. The ineffective assistance claim must first 

be presented to the BIA. Second, the dissent would eliminate the 

first prong of the BIA's judicially approved ineffective 

assistance standard requiring a showing of deficient performance. 

Third, the dissent alters the standard of judicial review from 

whether the BIA had substantial evidence on which to find deficient 

performance and instead would substitute a new standard of review 

in the guise of de novo review of fundamental fairness concerns. 

Nothing in Congress's choice to use the word "the" in any way 

negates or weakens the other explicit requirements in the statutory 

bar to such collateral attacks.

The dissent's interpretation of § 1326(d) would also 

multiply litigation and stress the already burdened federal 

immigration agencies. The dissent's rule would create a 

requirement that the government advance every conceivable basis 

for removal in the original NTA and litigate each basis in an 

immigration hearing, even where one ground for removal would 

suffice. Cf. Magasouba, 543 F.3d at 16. If not, as is the case 

for Castillo-Martinez, the government would have to re-notice and 

redo the original immigration hearing, even though no party 

disputes that Castillo-Martinez would likely be subject to 

mandatory removal again.
- 34 -

III.

Affirmed.

-Dissenting Opinion Follows-
- 35 -

BARRON, Circuit Judge, dissenting. This case concerns 

an order of removal entered against Jesus Leonardo CastilloMartinez nearly a decade ago. But, it is not about whether he may 

be removed pursuant to that order. It is about the criminal 

consequences that he may be subjected to under 8 U.S.C. § 1326, 

which makes it a felony to enter unlawfully the United States 

"while [an] order of . . . removal is outstanding." Id. § 1326(a). 

Castillo-Martinez contends that the indictment that 

charges him with that offense must be dismissed because the 

government may not use his prior removal order to prove the 

"outstanding order of removal" element of the crime that § 1326 

sets forth. He contends that the government may not do so because 

his counsel's assistance in the removal proceedings that produced 

that order was so deficient that it not only rendered them 

fundamentally unfair but also precluded him from subjecting them 

to judicial review in the first instance. He thus seeks to dismiss 

his indictment based on what amounts to a Due Process-based 

collateral attack on the order of removal that grounds his criminal 

prosecution. 

A criminal defendant, like Castillo-Martinez, can seek 

to dismiss his § 1326 charge by collaterally attacking the 

predicate order of removal on the ground that it resulted from 

fundamentally unfair administrative proceedings that also 

improperly prevented it from being judicially reviewed. The 
- 36 -

Supreme Court held as much in United States v. Mendoza-Lopez, 481 

U.S. 828 (1987), and Congress implemented that ruling in § 1326 

itself, by adding subsection (d) in the wake of the Court's ruling. 

That provision is entitled, "Limitation on collateral 

attack on underlying deportation order." 8 U.S.C. § 1326(d). It 

expressly provides that "[i]n a criminal proceeding under this 

section, an alien may not challenge the validity of the [prior] 

deportation order . . . unless the alien demonstrates": (1) that 

he "exhausted any administrative remedies that may have been 

available to seek relief against the order"; (2) that "the 

deportation proceedings at which the order was issued improperly 

deprived the alien of the opportunity for judicial review"; and 

(3) that "the entry of the order was fundamentally unfair." Id.; 

see also United States v. Palomar-Santiago, 141 S. Ct. 1615, 1620-

21 (2021).

The District Court assumed that Castillo-Martinez made 

the requisite showings under both (d)(1) and (d)(2), and the 

government does not contend otherwise on appeal. Thus, to hear 

the parties tell it, we need decide only one issue: can CastilloMartinez show under (d)(3) that the "entry of the order was 

fundamentally unfair"? 

The District Court explained that he could not do so for 

two reasons, and they are, as it happens, the only two reasons on 

which the government now asks us to rely to affirm the District 
- 37 -

Court. The first is that Castillo-Martinez did not in fact receive 

ineffective assistance of counsel, because his counsel's 

performance in connection with his removal proceedings was not 

constitutionally deficient. The second is that, even if CastilloMartinez did receive such constitutionally deficient assistance of 

counsel, the "entry of the order of removal" against him was still 

not "fundamentally unfair" within the meaning of (d)(3). 

As I will explain, neither reason holds up. The first 

depends -- at least given the limited nature of the District 

Court's ruling -- on a troubling view of the level of performance 

that may be expected of counsel that I do not understand our prior 

precedent to require. The second -- insofar as it truly differs 

from the first -- rests on both a mistaken understanding of the 

degree of prejudice that must be shown to establish a violation of 

the right to procedural due process and a construction of § 1326(d) 

that accords with neither its plain text nor its statutory history. 

Thus, I would vacate the District Court's order denying 

Castillo-Martinez's motion to dismiss his indictment. That way, 

the parties may hash out on remand any issues beyond those 

addressed by the District Court and presented to us by the 

government that might bear on whether the denial of the motion to 

dismiss the indictment is warranted.12 

12 I agree that there is no merit to Castillo-Martinez's 

collateral challenge to the validity of his underlying order of 
- 38 -

Ordinarily, there would be no need for me to address any 

of those potential issues. But, the majority has chosen, most 

unusually, to reach out to resolve some of them. Accordingly, I 

will address briefly the problems with the (unaided) ways in which 

the majority has done so before then addressing the issues that 

concern (d)(3), which in my view are the only issues that are 

properly before us in this appeal. First, though, it is necessary 

to review the Supreme Court ruling that is the genesis for 

§ 1326(d): Mendoza-Lopez.

I.

Decades ago, § 1326 provided that "[a]ny alien who --

(1) has been arrested and deported or excluded and deported, and 

thereafter (2) enters, attempts to enter, or is at any time found 

in, the United States . . . shall be guilty of a felony . . . ." 

8 U.S.C. § 1326 (1982). Criminal defendants seeking to block their 

prosecution for that offense sometimes brought collateral attacks 

on their predicate deportations to prevent their conduct (unlawful 

entry) from resulting in their being convicted of a felony rather 

than a misdemeanor. See Mendoza-Lopez, 481 U.S. at 841 n.18 

(explaining that "8 U.S.C. § 1325 . . . provides that an unlawful 

entry into the United States constitutes a misdemeanor" and that 

removal insofar as it rests on the contention that, per Pereira v. 

Sessions, 138 S. Ct. 2105 (2018), the Immigration Judge had no 

jurisdiction to enter it.
- 39 -

"[§] 1326 serves to enhance the penalty for unlawful entry, 

imposing a steeper punishment on individuals who violate § 1325 

and who have previously been deported"). 

The lower courts were divided over whether such 

collateral attacks could be brought, in large part because the 

version of the statute then in place did not contain -- as it now 

does -- a provision that recognized that such attacks were 

permissible. See id. at 833 n.6. Mendoza-Lopez helped to resolve 

a good deal of the confusion. 

The Court explained that § 1326 did not itself make the

validity, rather than the fact of the prior deportation, relevant 

to proving the prior-deportation element of the offense. See id.

at 834-37. But, the Court held that "[i]f [§ 1326] envisions that 

a court may impose a criminal penalty for reentry after any

deportation, regardless of how violative of the rights of the alien 

the deportation proceeding may have been, the statute does not 

comport with the constitutional requirement of due process." Id.

at 837 (emphasis in original). 

The Court explained that prior precedents had 

established "that where a determination made in an administrative 

proceeding is to play a critical role in the subsequent imposition 

of a criminal sanction, there must be some meaningful review of 

the administrative proceeding." Id. at 837-38 (emphasis in 

original). Thus, Mendoza-Lopez derived a relatively limited --
- 40 -

but still consequential -- due process holding: "at the very 

least . . . where the defects in an administrative proceeding 

foreclose judicial review of that proceeding, an alternative means 

of obtaining judicial review must be made available before the 

administrative order may be used to establish conclusively an 

element of the criminal offense." Id. (emphasis added). And the 

Court elaborated on that holding this way: "at a minimum, the 

result of an administrative proceeding may not be used as a 

conclusive element of a criminal offense where the judicial review 

that legitimated such a practice in the first instance has 

effectively been denied." Id. at 838 n.15 (emphasis added).13 

The Court then turned to the specific facts of the § 1326 

cases at hand. It "accept[ed]" the rulings by the courts below 

"that the deportation hearing [at issue] violated due process," 

id. at 840, because the government had "asked this Court to assume 

that respondents' deportation hearing was fundamentally unfair," 

id. at 839. It thus observed that there remained to resolve only 

whether "the violation of respondents' rights that took place in 

this case amounted to a complete deprivation of judicial review of 

the [administrative] determination." Id. at 840. For, if it did, 

13 The Court did note that, in some cases, the provision 

of a collateral means of judicial review would itself be incapable 

of addressing the concern, because the defects in the 

administrative proceedings might be of a structural nature that 

would inherently preclude any judicial review of them from being 

meaningful. See Mendoza-Lopez, 481 U.S. at 839 n.17. 
- 41 -

the Court explained, then "that [administrative] determination may 

not be used to enhance the penalty for an unlawful entry under 

§ 1326." Id. 

The Court pointed out that the government had conceded 

that there were defects in the deportation proceedings that 

rendered "fundamentally unfair" the entry of the deportation 

orders at issue. See id. The Court then explained that those 

defects also improperly precluded judicial review of those 

deportation proceedings, because the immigration judge failed 

adequately to apprise the § 1326 defendants in their immigration 

proceedings of both the option of seeking a suspension of 

deportation (which, if exercised, would have precluded the entry 

of the order of deportation that the government was using to prove 

the prior-deportation element of the § 1326 offense) and their 

appellate rights. See id. That failure, the Court found,

"permitted waivers of the right to appeal that were not the result 

of considered judgments by respondents, and failed to advise 

respondents properly of their eligibility to apply for suspension 

of deportation." Id. Thus, the Court held that it followed that 

the federal constitutional guarantee of due process precluded the 

government from "rely[ing] on those orders as reliable proof of an 

element of a criminal offense." Id. (emphasis added). 

The Court appeared to leave unresolved whether the 

defendant in a criminal proceeding would have to show that an 
- 42 -

administrative order had been entered in violation of due process, 

rather than merely unlawfully, to establish that the right to due 

process barred the government from using that order in the criminal 

proceedings as "reliable proof" of a crime's element.14 But, 

Castillo-Martinez grounds his right to challenge the validity of 

his underlying order of removal in § 1326(d). And, (d)(3), by 

requiring that he show that "the entry of the order was 

fundamentally unfair," plainly requires Castillo-Martinez to show 

that the entry of the order was at the very least the product of 

a due process violation.15

14 Notably, Mendoza-Lopez observed that, even if a 

collateral judicial-review "safeguard" were in place, "the use of 

the result of an administrative proceeding to establish an element 

of a criminal offense is troubling." Id. at 838 n.15. In so 

stating, the Court conceded that it had permitted an administrative 

order that was, by design, not subject to direct judicial review 

to be used to prove an element of a criminal offense in Yakus v. 

United States, 321 U.S. 414 (1944), but emphasized that the 

criminal prosecution there was for the violation of an 

administrative regulation that Congress had intentionally 

insulated from direct judicial review due to the exigencies of 

wartime and, "most significantly, . . . adequate judicial review 

of the validity of the regulation was available in another forum" 

in advance of the criminal proceedings predicated on that 

regulation. Mendoza-Lopez, 481 U.S. at 838 n.15.

15 By its terms, § 1326(d) imposes a "[l]imitation on 

collateral attack[s]" and specifies three necessary conditions 

that a defendant must satisfy in order not to be barred from 

collaterally attacking the "underlying deportation order." But, 

the parties in this case assume -- and I adopt their 

assumption -- that § 1326(d) also authorizes such attacks and that 

its three prongs, if satisfied, render a defendant's attack 

successful. 
- 43 -

So, for our purposes, the following questions are the 

only ones that are potentially at issue. First, has CastilloMartinez shown that, based on the ineffective assistance of counsel 

that he claims to have received in his 2013 removal proceedings, 

he was "improperly deprived . . . of judicial review" within the 

meaning of (d)(2)? Second, has he also shown, on that same basis, 

that he did all that he was expected to do to satisfy (d)(1)'s 

requirement to exhaust available administrative remedies? And, 

third, if he has shown that much, has he has shown as well -- as 

he must under (d)(3) -- that the "entry of the order [of removal] 

was fundamentally unfair"? 

II.

There is not much that I need to say about whether 

Castillo-Martinez has shown what he must to satisfy the first two 

requirements set forth in § 1326(d). The District Court assumed 

that he had, and the government does not ask us to revisit that 

assumption. Nevertheless, the majority chooses of its own accord 

to hold that Castillo-Martinez's bid to dismiss his indictment 

fails under both (d)(1) and (d)(2). I thus begin by explaining my 

concern with this aspect of the majority's decision.

As an initial matter, nothing indicates that either 

(d)(1) or (d)(2) constrains our subject matter jurisdiction. In 

Mendoza-Lopez itself, moreover, the Court relied on the 

government's concession that the underlying immigration 
- 44 -

proceedings were "fundamentally unfair" rather than on its own 

independent (and unargued for) determination of whether they were. 

481 U.S. at 839-40. Thus, it seems to me that the majority is 

excusing the government's failure to make arguments regarding 

(d)(1) and (d)(2) even though the government has not itself asked 

us to do so.

To be clear, I am not suggesting that the government has 

conceded that the relevant requirements have been met merely by 

failing to argue otherwise to us. See Maj. Op. at 27 n.9. But, 

I do note that the government's opposition to Castillo-Martinez's 

motion to dismiss failed to address his developed contention below 

that he should be treated as having satisfied both (d)(1) and 

(d)(2) because the ineffective of assistance of counsel that he 

contends that he received in his removal proceedings prevented him 

from raising that contention in his removal proceedings and 

effectively rendered him unable to have the issue reviewed on 

appeal. Thus, the majority is necessarily relying on an 

independent ground for affirming the District Court that the 

government failed to develop any argument in support of at any 

point in this litigation. 

I suppose such reliance would be less concerning if it 

were clear that Castillo Martinez had not met the two requirements 

at issue. But, the majority offers no explanation for how 

Castillo-Martinez could have successfully raised his claim of 
- 45 -

ineffective assistance of counsel in his removal proceedings, 

while its only arguments in support of its conclusion that 

Castillo-Martinez cannot show that he exhausted his available 

administrative remedies directly conflict with the only relevant 

circuit-level authority. See United States v. Lopez-Chavez, 757 

F.3d 1033, 1044 (9th Cir. 2014); United States v. Cerna, 604 F.3d 

32, 40 (2d Cir. 2010); Maj. Op. at 13-14.16 I note, moreover, that 

Mendoza-Lopez -- which was the catalyst for Congress's enactment 

of § 1326(d) -- found merit to the collateral challenge in the 

criminal proceeding there at issue without addressing whether any 

administrative collateral challenge had been pursued. 

Nor does United States v. Palomar-Santiago, 141 S. Ct. 

1615 (2021), provide the missing clarity. The Supreme Court did 

hold that the three requirements of § 1326(d) are conjunctive. 

Id. at 1620-21. It did not address, however, what the majority 

now resolves on its own -- what would suffice to demonstrate that 

two of them had been satisfied? 

16 I understand the majority's assertion that CastilloMartinez failed to comply with (d)(1) because he failed to comply 

with the requirements for lodging a claim of ineffective assistance 

set forth by the Board of Immigration Appeals in Matter of Lozada, 

19 I. & N. Dec. 637 (BIA 1988), Maj. Op. at 15-18, to depend on 

the majority's contention that (d)(1)'s reference to the 

exhaustion of remedies encompasses motions to reopen.
- 46 -

III.

I come, then, to the question of whether CastilloMartinez can satisfy the requirement set forth in (d)(3). He 

contends that he can because his counsel's assistance in his 

removal proceedings was so ineffective that it rendered them 

fundamentally unfair. He thus contends that he can successfully 

collaterally attack his prior order of removal, such that the 

government cannot now rely on that order as "reliable proof," 

Mendoza-Lopez, 481 U.S. at 840, of the "outstanding order of 

removal" element of the criminal offense that § 1326 sets forth, 

id. at § 1326(a). 

The government does not dispute on appeal that a 

noncitizen may be deprived of his right to due process under the 

Fifth Amendment in removal proceedings in consequence of his 

counsel's ineffective assistance in them. Muyubisnay-Cungachi v. 

Holder, 734 F.3d 66, 72 (1st Cir. 2013). There is thus no dispute 

on appeal that the provision of ineffective assistance of counsel 

in removal proceedings can, at least in some circumstances, render 

them fundamentally unfair within the meaning of (d)(3). See

Fustaguio Do Nascimento v. Mukasey, 549 F.3d 12, 17 (1st Cir. 2008) 

("Ineffective assistance of counsel in a deportation proceeding is 

a denial of due process under the Fifth Amendment if the proceeding 

was so fundamentally unfair that the alien was prevented from 

reasonably presenting his case." (quoting Rodríguez–Lariz v. INS, 
- 47 -

282 F.3d 1218, 1226 (9th Cir. 2002))). Accordingly, I now turn to 

the dispute before us, which concerns only whether CastilloMartinez can show that he received ineffective assistance of 

counsel of that kind in his removal proceedings. 

A.

The District Court ruled that Castillo-Martinez has not 

shown that he was deprived of procedural due process because he 

has not shown that his counsel's performance in those proceedings 

was constitutionally "deficient." See Muyubisnay-Cungachi, 734 

F.3d at 72. That is so, according to the District Court, even 

though his counsel in those proceedings conceded his removability 

as an "aggravated felon" under 8 U.S.C. § 1101(a)(43) based on his 

prior state law marijuana conviction. The District Court explained 

that its conclusion followed from the fact that such a concession 

was supported at the time by then-controlling First Circuit 

precedent, see Julce v. Mukasey, 530 F.3d 30, 35 (1st Cir. 2008), 

abrogated by Moncrieffe v. Holder, 569 U.S. 184 (2013), and the 

majority endorses that same conclusion, noting that it is clear 

under our precedent that, absent "unusual circumstances," "an 

attorney's assistance is not rendered ineffective because he 

failed to anticipate a new rule of law," Powell v. United States, 

430 F.3d 490, 491 (1st Cir. 2005) (quoting Kornahrens v. Evatt, 66 

F.3d 1350, 1360 (4th Cir. 1995)); Maj. Op. at 20. 
- 48 -

But, the record shows that the circumstances in this 

case were "unusual." At the very moment that Castillo-Martinez's 

counsel was conceding that his client could lawfully be removed 

based on his prior marijuana conviction, the Supreme Court was 

poised to render a decision, in a case that had already been 

argued, that would make clear that he could not be. See Moncrieffe

v. Holder, 566 U.S. 920 (2012) (granting the petition for writ of 

certiorari); Transcript of Oral Argument, Moncrieffe, 569 U.S. 184 

(No. 11-702), 2012 WL 4812587 (identifying the oral argument date 

as October 10, 2012). Moreover, there was at that time a circuit 

split among five courts of appeals on the question of whether a 

prior conviction for distributing marijuana (which was what 

Castillo-Martinez's prior conviction was for) qualified as an 

"aggravated felony" within the meaning of 8 U.S.C. § 1101(a)(43), 

with two circuits taking the opposite view from our circuit's 

ruling on that question in Julce. See Moncrieffe, 569 U.S. at 190 

n.3. And, what is more, there was intervening Supreme Court 

precedent that had already undercut Julce.17 

17 Julce had reached the conclusion that it did by 

applying a circumstance-specific "'hypothetical federal felony' 

approach" to determine whether a state conviction qualifies as an 

aggravated felony under the INA. 530 F.3d at 33 (quoting Berhe v. 

Gonzales, 464 F.3d 74, 84 (1st Cir. 2006)). But, in the wake of 

that ruling, the Supreme Court had indicated -- in Nijhawan v.

Holder, 557 U.S. 29 (2009) -- that we should instead be applying 

the categorical approach. See id. at 37 (noting that the phrase 

"illicit trafficking in a controlled substance" in the "aggravated 

felony" statute "must refer to [a] generic crime[]" and therefore 
- 49 -

Thus, I see no merit in the only ground that the District 

Court has given for ruling that Castillo-Martinez fails to show 

that his counsel provided constitutionally deficient assistance to 

him: that his counsel could not be expected to anticipate the new 

rule of law that favored his client. Cf. Lopez-Chavez, 757 F.3d 

at 1043 (concluding that counsel was ineffective in conceding 

removability where the removal order was based on the sole ground 

that the defendant's state law marijuana offense was an aggravated 

felony because that very issue was an open question in the 

applicable jurisdiction at the time of the order); United States

v. Castro-Taveras, 841 F.3d 34, 47 (1st Cir. 2016) (explaining 

that "'[d]efense counsel too must know or learn about the relevant 

law and evaluate its application to his or her client'" and that 

"failure of knowledge by counsel" as to "the 'most fundamental 

statutory provision relating to sentencing' . . . may 'amount to 

constitutionally ineffective assistance of counsel'" (alteration 

in original) (quoting Correale v. United States, 479 F.2d 944, 949 

(1st Cir. 1973))). Accordingly, I would vacate the District 

Court's ruling, insofar as it is dependent on this finding of no 

"deficient performance." That way, the District Court may 

calls for the "categorical approach"); see also Moncrieffe, 569 

U.S. at 192 ("The aggravated felony at issue here, 'illicit 

trafficking in a controlled substance,' is a 'generic 

crim[e].' . . . So the categorical approach applies." (quoting 

Nijhawan, 557 U.S. at 37)).
- 50 -

determine in the first instance if there is some other basis (still 

viable in the case) for finding that Castillo-Martinez has not 

shown what he must under the "deficient performance" component of 

his ineffective assistance of counsel claim. 

I do recognize that the majority would have us bypass 

this conventional method of appellate adjudication, as the 

majority reaches out on its own to rule that Castillo-Martinez 

received constitutionally adequate assistance from his counsel in 

his immigration proceedings on a ground that the District Court 

did not address and that the government neither presses in this 

appeal nor advanced below. The majority asserts in this regard 

that Castillo-Martinez's counsel may reasonably be understood to 

have made a strategic choice not to press the Moncrieffe point.

In support of that contention, the majority asserts that 

Castillo-Martinez's counsel may have reasonably assessed that the 

Moncrieffe argument ultimately would have offered no aid to 

Castillo-Martinez because an order of removal could have been later 

entered against him either on the ground that he was an "aggravated 

felon" based on his 2012 OxyContin conviction in New Hampshire, 

see 8 U.S.C. § 1227(a)(2)(A)(iii), or on the ground that he was 

not entitled to be spared from removal for having unlawfully 

entered the country initially based on a discretionary 

determination predicated on his marijuana conviction. Maj. Op. at 

20-22. For that reason, the majority concludes, Castillo-
- 51 -

Martinez's counsel acted competently in pressing only a claim under

the Convention Against Torture, as that claim alone would have 

stood in the way of his removal on either of those alternative 

grounds. 

But, neither the government nor the District Court has 

suggested that Castillo-Martinez's counsel was not 

constitutionally deficient in failing to advance the argument that 

won the day in Moncrieffe because he was in fact savvy for failing 

to have done so. They have asserted (unpersuasively in my view) 

only that he was not constitutionally deficient in failing to 

advance that argument because he was excusably lacking in 

foresight. Castillo-Martinez was not apprised at any prior point 

in the litigation that the competency of his counsel was being 

disputed on that basis. Nor have we sought supplemental briefing 

to see what he might have to say about it now that it is being 

disputed. I thus cannot agree that it is proper for us to reject 

Castillo-Martinez's claim of ineffective assistance of counsel on 

this alternative "strategic choice" ground. 

B.

Of course, Castillo-Martinez must show more than that 

his counsel's performance in his removal proceedings was 

constitutionally deficient to succeed on his due process-based 

collateral attack on the removal order that grounds his prosecution 

under § 1326. He must also show that such poor performance 
- 52 -

"prevented [him] from reasonably presenting his case." Fustaguio 

Do Nascimento, 549 F.3d at 17 (quoting Rodríguez–Lariz, 282 F.3d 

at 1226). The District Court and the majority each concludes that 

he cannot make that showing either. Here, as well, I am not 

persuaded. 

The sole legal basis for the only order of removal that 

was entered against Castillo-Martinez was that he qualified as an 

"aggravated felon" under Sections 101 and 237 of the Immigration 

and Nationality Act. See 8 U.S.C. §§ 101(a)(43)(B), 

1227(a)(2)(A)(iii). That order based that conclusion solely on 

the fact that he had been convicted of the offense of marijuana 

possession under Massachusetts law. Yet, as I have explained, 

Moncrieffe makes clear that such an order is unlawful. Thus, it 

would appear to me that Castillo-Martinez can show that his 

counsel's failure to raise the Moncrieffe-related argument did 

prevent him from reasonably presenting the case that it would be 

unlawful to order him removed on the sole ground on which his order 

of removal rested.

The District Court and the majority conclude, however, 

that Castillo-Martinez must show that no other order of removal 

could have been entered against him. They then conclude that he 

has not done so, because the record shows that he could have been 

ordered removed (even though he was not) at those same immigration 

proceedings based on either his separate OxyContin conviction or 
- 53 -

a discretionary determination keyed to the marijuana conviction 

itself. Maj. Op. at 23-25.

The prospect that a removal order premised on either 

ground could have been entered (but was not) might support the 

conclusion that his counsel reasonably surmised that a Moncrieffebased challenge would merely delay the inevitable. It thus might 

support an argument that his counsel acted strategically and so 

not deficiently. But, insofar as the District Court and the 

majority mean to make a point about the prejudice that the Fifth 

Amendment right to procedural due process generally demands, I 

cannot see why that prospect is of note. 

If Castillo-Martinez had been ordered removed solely on 

the basis of his prior state-law marijuana conviction after

Moncrieffe, and he then petitioned to have it vacated based on 

that ruling, we would not deny his petition for review and leave 

his plainly unlawful order of removal in place just because the 

record showed that he could have been ordered removed -- but was 

not -- based on his OxyContin conviction or a discretionary 

decision to deny him relief based on his prior marijuana 

conviction. Why, then, should the fact that the claimed reason 

for deeming the entry of the order of removal to have been unlawful 

is that it violated the Fifth Amendment in and of itself require 

us to reach a different conclusion?
- 54 -

Consider the case of the non-English speaking child who 

is ordered removed on a plainly unlawful basis in an uncounseled, 

untranslated proceeding. Does her due process-based challenge to 

the resulting removal order come up short, such that she may be 

removed from the country pursuant to the only order of removal 

actually entered against her (unlawfully entered though it was), 

so long as a reviewing court can scan the record and find that a 

different but lawful order of removal could have been entered and 

then asserted as the basis for her removal?

The majority contends that Williams v. United States, 

858 F.3d 708, 716 (1st Cir. 2017) supports its view that prejudice 

under the Fifth Amendment turns not on whether orders actually 

entered might have been unlawful but instead on whether orders 

never entered might have been lawful. Maj. Op. at 32-33. But, it 

does not. In Williams, a criminal defendant unsuccessfully sought 

to have his lawful conviction on one charge overturned on the 

ground that his counsel's ineffective assistance prevented him 

from being convicted unlawfully based on a different charge. Id.

at 716. I do not see how that precedent provides any support for 

the majority's notion that a never-entered, lawful order of removal 

necessarily suffices to make up for an unlawful one that was 

entered. 

The majority also points as support for its view of Fifth 

Amendment prejudice to Rivera-Rivera v. United States, 827 F.3d 
- 55 -

184 (1st Cir. 2016), which holds that prejudice under Strickland

v. Washington, 466 U.S. 668 (1984), requires a showing that the 

"result of the criminal proceeding would have been different' if 

counsel had performed as the defendant asserts he should have." 

Rivera-Rivera, 827 F.3d at 187 (quoting Hensley v. Roden, 755 F.3d 

724, 736 (1st Cir. 2014)); Maj. Op. at 31. But, nothing in RiveraRivera suggests that the "result" that the court had in mind was 

a conviction that could have been entered but was not rather than 

the actual conviction that was the subject of the defendant's 

challenge. See Rivera-Rivera, 827 F.3d at 187 (finding no 

prejudice where counsel's failure to move for a judgment of 

acquittal did not affect the outcome of the case because the motion 

would have failed and the conviction would have stood). For that 

reason, it adds nothing to point out, as the majority does, that 

there must be a substantial likelihood that the "result" would be 

different here, because Moncrieffe makes clear that the only 

removal order that was entered could not have been lawfully 

entered.

The majority, finally, suggests that, precedent aside, 

efficiency provides support for embracing its view of prejudice. 

It explains that a prejudice rule that prevents an unlawful removal 

order from being given effect when it is clear that a lawful order 

could have been entered in its stead will force the government 

either to restart the removal proceedings all over again for no 
- 56 -

good reason or to load up on grounds for removal from the get go. 

Maj. Op. at 33-34. 

But, I would have thought that such "inefficiency" is 

more of a feature than a bug of the attractive way in which we 

have chosen to organize our system of administrative adjudication. 

It ensures that a consequence as serious as expulsion from the 

country follows from an actual lawful order and not merely a 

hypothetical one that was never entered at all.

In any event, insofar as efficiency is our guide, the 

majority's approach hardly promotes it. Under its approach, must 

a defendant -- or a court -- in an unlawful reentry proceeding 

anticipate and refute every conceivable legal ground that the 

government could have attempted to predicate an order of removal 

on when seeking the removal of that individual, notwithstanding 

that "the order" of removal that was actually entered and that is 

the only one that "is outstanding" at the time of the alleged 

unlawful reentry is the product of constitutionally deficient 

legal assistance? And if not, what are the limits on either the 

defendant's or the court's obligation to account for those 

possibilities? 

The more straightforward view of prejudice that grounds 

Castillo-Martinez's motion to dismiss his indictment ensures that 

such time-consuming hypothetical inquiries need not be undertaken. 

It directs the reviewing court to focus not on a might-have-been 
- 57 -

world of non-existent orders but on something readily discernable 

-- the lawfulness of the administrative order that was in fact 

entered and that the government seeks to use to prove its criminal 

case.

C.

The majority and the District Court do each separately 

also conclude that Castillo-Martinez cannot make the requisite 

showing of prejudice under (d)(3). Perhaps in doing so the 

majority and the District Court mean to assert nothing more than 

that, because Castillo-Martinez cannot show the requisite degree 

of prejudice under the Fifth Amendment, he cannot show the degree 

of prejudice required by this statutory provision. If so, then 

their contention fails for all the reasons that I have just given. 

But, if they mean to suggest that (d)(3) imposes a more onerous 

prejudice requirement than the one that the Fifth Amendment imposes 

of its own accord, then I cannot agree. 

The use of the definite article "the" in "the entry of 

the order" gives little hint that there is a need to show that 

"the entry of any order of removal" that the immigration judge 

could have issued in those proceedings but did not would have been 

"fundamentally unfair." Indeed, the use of the phrase "the entry" 

further underscores that point by doubling down on the provision's 

use of the definite article and imposing "a temporal limitation on 

the . . . court's inquiry" to ensure "that § 1326(d)'s prejudice 
- 58 -

inquiry does not extend beyond the fairness of the deportation 

order itself." United States v. Scott, 394 F.3d 111, 118-19 (2d 

Cir. 2005). 

That "the order" referenced in (d)(3) would appear to be 

the same "order" referenced in subsection (a) reinforces the same 

conclusion. A hypothetical order of removal that never was cannot 

be "an order . . . that is outstanding" at the time the unlawful 

reentry occurs, id. at § 1326(a). 

Nor do the words "fundamentally unfair" in (d)(3) 

suggest otherwise. I suppose the notion must be that those words 

may be read to imply that the actual order that was 

entered -- though itself unreliable proof of that element due to 

its insulation from judicial review and the unfairness of the 

proceedings that produced it -- may spring back into respectability 

whenever the record shows that some other order could have been 

entered to take its place. If so, I guess the further notion must 

be that the words "fundamentally unfair" in (d)(3) may be read to 

imply that the tainted and unlawful order may be used in that event 

to prove the crime without thereby causing any fundamental 

unfairness, because we can be confident that a different (though 

never entered) order could have taken its place. 

But, to describe that notion of why reliance on the 

tainted (and never judicially reviewed) order of removal is not 

fundamentally unfair is to undermine it. The phrase itself --
- 59 -

"fundamentally unfair" -- is plainly included to ensure that the 

provision accords with Mendoza-Lopez. The due process concern 

that the Court identified there, however, inhered in the 

government's use of administrative orders as if they were "reliable 

proof" of an element of a criminal offense, even when those orders 

resulted from fundamentally unfair administrative proceedings that 

had never been judicially reviewed. The Court at no point 

suggested that such a concern would disappear just because some 

other more reliable means of proving that element of the criminal 

offense could have existed but does not.18 

In this respect, purpose would seem to confirm what text 

indicates. The surest way to prevent what concerned the Court in 

Mendoza-Lopez from occurring in § 1326 prosecutions is to prevent 

the government from relying on an order entered in violation of 

due process -- and insulated from intended direct judicial review 

-- to prove an element of the unlawful reentry offense.

Finally, this easy-to-implement understanding of (d)(3) 

is not mine alone. See United States v. Martinez, 786 F.3d 1227, 

18 Nor can Mendoza-Lopez's references to structural 

defects that are preclusive of all judicial review be read to 

suggest that such defects must be shown under (d)(3)'s 

"fundamentally unfair" prong. In addition to the fact that nothing 

in Mendoza-Lopez itself suggests that defects of that type must be 

shown, (d)(2) independently requires a showing that the underlying 

administrative proceedings "improperly deprived" the § 1326 

defendant of "judicial review" of "the order" entered in them and 

so would be superfluous if (d)(3) were so read.
- 60 -

1232-33, 1233 n.2 (9th Cir. 2015); Lopez-Chavez, 757 F.3d at 1043 

("[H]ad counsel presented the Seventh Circuit with the question of 

which rule to adopt, [the defendant's] order of removal would have 

been held unlawful and would not have gone into effect. Thus, 

[the defendant's] counsel's ineffectiveness not only may have 

affected, but actually did, 'affect[] the outcome of the 

proceedings.'" (last alteration in original) (footnote omitted) 

(quoting Correa-Rivera v. Holder, 706 F.3d 1128, 1133 (9th Cir. 

2013))); United States v. Camacho-Lopez, 450 F.3d 928, 930 (9th 

Cir. 2006) ("[Defendant's] Notice to Appear charged him as 

removable only for having committed an aggravated felony; . . . 

[because his] prior conviction did not fit that definition . . . , 

[he] was removed when he should not have been and clearly suffered 

prejudice."); Scott, 394 F.3d at 118-19. But see United States v. 

Martinez-Hernandez, 932 F.3d 1198, 1204 (9th Cir. 2019) (holding 

that the erroneous classification of predicate convictions as 

crimes of violence under 8 U.S.C. § 1101(a)(43)(F) did not render 

the defendants' NTAs invalid because those convictions could have 

been classified instead as theft offenses under 8 U.S.C. 

§ 1101(a)(43)(G), which also would have made the defendants 

removable as aggravated felons); United States v. Almanza-Vigil, 

912 F.3d 1310, 1323 n.10 (10th Cir. 2019). And insofar as this 

Court's decision in United States v. Soto-Mateo might be read to 

take the opposite view, it does so only in dicta and without 
- 61 -

considering the Ninth Circuit's alternative approach. See 799 

F.3d 117, 124 (1st Cir. 2015). 

IV.

For all these reasons, then, I am not persuaded that 

either the District Court or the majority has provided a sound 

reason for concluding that Castillo-Martinez has failed to show 

what he must to satisfy § 1326(d). I thus would vacate and remand 

the District Court's order denying his motion to dismiss his 

indictment. By following that approach, we would ensure that 

whatever arguments remain for denying the motion may be considered 

in the ordinary course and thus only after full contestation 

between the parties. We also would ensure that, in deciding 

whether to permit this criminal prosecution to go forward, we would 

not be unnecessarily and unduly cabining the protections afforded 

by the Fifth Amendment to those facing removal and by § 1326(d) to 

those facing criminal prosecution for the crime of unlawful reentry. 

Accordingly, I respectfully dissent.